
House vacation rentals in Chester
Find and book unique houses on Airbnb
Top-rated house rentals in Chester
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chester house rentals
House rentals with a pool

Beautiful country house with 5 bedrooms 4.5 baths
Absolutely beautiful place to stay. We enjoyed everything the home offered. Lots of things for the kids to do. My daughter enjoyed the pool very much! The home and property were better in person. Super clean and comfortable beds. I would definitely recommend and will return for sure!

Pool/Hot tub/Entire House 2100 Sq ft
Comfortable home that was exactly what my family needed. The rooms were spacious and beds comfortable. Shower on the first floor is my favorite of any place I’ve stayed. Maria was always responsible and was flexible my with requests.

Brydie’s Suite at Meremont
Highly Recommend! This place is even more beautiful in person! Super clean, cozy, and peaceful. The pool, jacuzzi, and view were amazing.we spent hours relaxing and enjoying the sunshine and omg the sunset is beautiful. The bed and couch were so comfy. our Yorkie loved running around the big yard. The area is quiet and perfect for a getaway. We enjoyed a great BBQ by the pool, and everything was just perfect,very private too. Melissa is a fantastic host,very friendly and quick to respond. Don’t hesitate to book, you’ll love it here! we drove 7 hrs+ from NYC it was worthy,definitely booking again!! Thanks for everything Melissa. Best, Brian,Kennia &Coco 🐶

Historic Blanton Getaway
This place was great! The location makes it easy to get to many places in Richmond quickly and it was a perfect location for a family wedding in nearby Maymont. The house is beautiful and the furnishings very comfortable. The pool was a special bonus - lovely and relaxing with incredible plantings. Clearly a lot of time was spent considering what guests might want. I just wish we'd had more time to enjoy it.

Artfully Elegant Getaway
Shannon’s place met our expectations. The price for our stay was more than reasonable. It’s such a quiet and calming space. Everything was super clean, and the neighbors were super friendly. Would 100% recommend it!

A house you wish you called home
Good communication, great value, and flexible with a small adjustment that was needed. I would definitely stay there again.

The Resort
The Resort was a lovely home on a quiet street. Beautifully furnished and comfortable. Backyard was small but very well done with a pool and lots of seating. Host was friendly and responded quickly. We would definitely recommend staying here!

Lakefront Resort
This house is awesome. It's huge and priced very competitively. It did have issues, but they didn't bother us too much. If you're expecting perfection from a home this size, at this location at this price, you're not being reasonable. For our needs, it was PERFECT.
Weekly house rentals

City Point Cottage
City Point Cottage was all that we hoped it would be based on the listing and more!! The most beautiful renovations and just our style! City Point Cottage was in the perfect spot to visit my son at Ft Gregg - Adams! Caroline was an excellent host, very responsive and very clear instructions for check in/out and instructions for inside the cottage! Very cute place!

The Duck Blind located near RIC airport
Stayed at the Duck Blind for the weekend, the house was perfect for my husband and I. Very clean and had everything we needed. Would definitely stay again if in the area.

Brand-New Boho Family Getaway!
Perfect Haven! Loved the home. It was exactly what we needed. Lot's of space for a large family. All the amenities we needed and close to everywhere we needed to go. We truly enjoyed our stay.

4 Bedrooms House
Our family recently enjoyed a wonderful stay in your spacious and comfortable home. It was perfectly sized for our needs, providing ample room for everyone. We were particularly impressed by the thoughtful provision of all necessary amenities, making our stay incredibly convenient and relaxing. The peaceful location was a welcome respite, offering a tranquil atmosphere we thoroughly appreciated. The cleanliness of the property was exceptional, contributing significantly to our overall positive experience. Thank you for providing such a welcoming and well-maintained home for our family weekend. We would highly recommend your property to others.

Fenced Yard, Swing Set: Pawfect for Family & Dogs!
The house was absolutely perfect and comfortable for our family! It was very clean and the beds, linens and towels were great! I will say that the one “bedroom” listed with a full bed is actually a laundry room with a bed in it off the kitchen. It turned out great for my granddaughter b/c she’s used to dark rooms but I wouldn’t necessarily list it as a bedroom for adults. Other than that, it was amazing! James was very responsive when I had some questions! Would definitely rent again if we are in the area!

Cupid's Hideout
Alexander was a wonderful host. Very responsive and helpful. Check in was a breeze. This was located in a prime location. Tons to do within walking distance. Many excellent restaurants in the area. I highly recommend El Pope, Beauvine, Abi’s Books & Brews, and Little Mexico! The home was beautiful!!! Absolutely stunning in person. Very clean. Great amenities! It is a hidden gem! There’s tons to do if you want to drive as well. Very cute area. Well worth it!! Thank you!!

Private 2 acres. Huge yard/drive. 8 min to Airport
Great value, close to Richmond, and great communication! Home was very clean and organized!

Hot Tub Oasis, Minutes from Downtown Richmond
Clean home, safe quiet neighborhood, wonderful back yard to relax very peaceful. Had everything you can possibly need. Huge kitchen. Close to restaurants and planet fitness right down the street. Any question I had the host (Elizabeth) responded right away, very kind. We loved our stay. Thank you!
Private house rentals

House full of peace, with a parking patio for 4 cars
We had a very comfortable and enjoyable stay. This older home in a quiet older neighborhood is well-maintained, thoughtfully updated, cozy, and comfortable. It was spotlessly clean, and the check-in process was a breeze. We appreciated the ample off-street parking and the layout, which easily accommodated the multiple generations of our family during our gathering in Richmond. Plus, the location was ideal—less than 15 minutes to downtown. Mayra, our host, made us feel very welcome and was quick to respond to any questions. The home was well stocked with everything we needed. (including a crib and bassinet) There is a large private fenced backyard and a nice office area. I would certainly stay here again.

Spacious home near downtown RVA
My family needed a place within the area to stay while emergency work was being performed on our home. Booking Mateo's place was painless and easy. Mateo's place had everything we needed and was very clean, tidy, and comfortable. Mateo was a very gracious host, always friendly and responsive. I would definitely recommend Mateo's home.

2-Bedroom oasis in Chesterfield
Ashley was amazing! When I told some issues she came and looked into it and fixed it ASAP. (Issue was very minor). The layout was great, sofas comfortable enough that you could sleep on them! Backyard was great for my two large dogs! Ashley was great! This is a perfect place for temporary housing or for like me for in between houses where I sold and had to wait a couple weeks until I could get into my new place!

Elegant Retreat: Spacious with Outdoor Fireplace
James place was very inviting. Loved sitting out on the back porch. Everything was spotless and we loved the decor. Host was very responsive and very helpful. They had a basket that had some much appreciated snacks as we got in a little late. There is a huge lovely park close by called Dorey park that you should go to. We will definitely return if we are ever in the area again.

Charming Bungalow in the Heart of Richmond
Mary Kristina was a great host! Instructions were very clear and she was very helpful and responsive. The house was beautiful too!

Exquisite Farmhouse Style Home
Close to Swim RVA and the soccer fields. much more convenient than staying on Midlothian Turnpike...and no traffic! Everyone had their own bed, and it's so nice for the adults to be able to stay up when the swimmers are early to bed early to rise. The place was clean, and we look forward to staying there again!

Modern Artsy Haven with Coffee/Snack Bar/King bed
This place is great the decor is A1 the master bedroom is simply amazing the soaker tub was a really nice touch the access to snacks,water,coffee & juice was a added bonus adequate space for a party of 5 the upstairs has its own living room which was nice for my kids to hang out I am super impressed

Entire Cozy Home in Richmond
"I loved my stay! The place was cozy and well-kept, with everything I needed. My host was super helpful and provided great recommendations for local attractions and activities. I felt right at home. Highly recommend!"
Quick stats about house rentals in Chester
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ110 before taxes and fees
Total number of reviews
410 reviews
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Kroger, Lowe's Home Improvement, and Sonic Drive-In
Destinations to explore
- Virginia Beach Vacation rentals
- James River Vacation rentals
- Western North Carolina Vacation rentals
- Myrtle Beach Vacation rentals
- Charlotte Vacation rentals
- Outer Banks Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- Pocono Mountains Vacation rentals
- South Jersey Vacation rentals
- Jersey Shore Vacation rentals
- New York Vacation rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Busch Gardens Williamsburg
- Carytown
- Kings Dominion
- Water Country USA
- Kingsmill Resort
- Pocahontas State Park
- Brown's Island
- Jamestown Settlement
- Hollywood Cemetery
- Science Museum of Virginia
- Royal New Kent Golf Club
- Independence Golf Club
- The Country Club of Virginia - James River
- The Foundry Golf Club
- Golden Horseshoe Golf Club
- Kinloch Golf Club
- Libby Hill Park
- NGCOA Mid-Atlantic
- Kiskiack Golf Club
- Grand Prix Raceway
- The Poe Museum